He was always going to be in a good position to make a smooth transition away from football once his dream came to an end.
After playing for non-League Cambridge City as a teenager, he studied for a degree in sports science and mathematics at Loughborough University and signed for Championship side from Cambridge United in July 2007, the same month as his graduation.
It was on the very first day of pre-season training that a seed was planted.
I heard Stephen Hughes and Arjan de Zeeuw say it could be their last season and wondered what they were going to do after football.
I thought to myself, "You must be a millionaire and not have to worry about working again!"
I was the only one with any form of education in the changing room as people got to know me. They were looking at me with a bit of jealousy because they thought I'd be fine when I got my degree. It was quite strange.
After two years with the Sky Blues, Simpson moved on to the Terriers but struggled for playing time and spent 18 months at the Latics in League One.
He was at Boundary Park in the summer of 2013).
He admits that he had always regretted dropping into League One after he left Coventry. It was going to be my last chance to return to the Championship.
I tried out for Championship clubs all summer but nothing came of it. I turned down offers from both League One and League Two clubs, but nothing came from Doncaster, or any of the other clubs.
I could see that it was coming down because I was still living the same lifestyle even though I had invested a lot and saved a lot.
When I turned down the offers from League One and Two clubs, I was in a bit of a hole. I didn't know what I wanted to do after football, so I didn't think I'd have to think about it until I was in my 30s.
I didn't think there was any support for that from any of the people.
After being told there were 2,000 candidates completing their badges and around 200 roles on offer, he didn't fancy a coaching career or a sports journalism course.
LAPS was created when there was a professional sport.
Simpson says that a few friends told him that he needed to get a profile on the professional networking site.
We met six months after I re-signed for Cambridge. I was asked by him if I knew how he could get to sports people, as he was a recruitment consultant for several companies. I wasn't sure why.
"He started listing off all the different attributes top-level sports people have: they are driven, they are determined, they are good goal-setters, they learn from failure quickly, and they analyse their own performance really well." He was correct about everything. If you want to become a professional sports person, you need to show a lot of these attributes.
There is a need for more support from the sportsperson's perspective in terms of the end of their career and what they are going to do after that. There is a need for companies to get into this market of sports people. It was very similar to a match in heaven.
LAPS was supposed to be a job board where he would go out and find companies to hire sports people on an online platform. If sports professionals saw something they liked on the online platform, they could log onto it and apply.
We realized that wasn't going to suffice. These guys wouldn't have written a CV since they were 16 because I hadn't written one since leaving university. 99% of football players didn't have a degree, so we needed to write CVs. We had to create a page to help them with interview techniques because none of them had ever been to an interview before.
Making sports people realize that the earlier they plan, the easier it will be at the end is the hardest thing.
They made it clear to members that they have anything up to 60 more years in which to sustain themselves and their families, but that they will do everything they can to find something that suits their needs.
There is a section on the LAPS website dedicated to video interviews with former sports people who have successfully transitioned into new and rewarding careers.
The Premier League and League Football Education requested a workshop that could be delivered to U18 and U23 teams and paid for by a portion of their annual education budgets.
Simpson doesn't mind that there can be mixed responses. I don't care if we don't hit 99 percent of the athletes we are talking to, because that one per cent matters and that one per cent makes it all worthwhile.
He has a success story that sticks in his mind.
"As soon as I set up LAPS, I told my team-mates about it down at Exeter and there was a lad called Tom McCready who was struggling to get a new club," he says.
He reached out to me after I established LAPS. St James' Place, the wealth management company, hosted the members meet-up because one of our partners hosted it in their office. I told Tom we had an open day and he showed up right away.
He listened to what St James' Place had to say about what a career in sports would look like. He called me the next day and said that he was going to look into it and see if I could get him in touch with them.
He has been with them for nearly five years, after we helped him get into their academy.
There is an ambition to join forces with the PFA, but so far no progress has been made on that front.
Simpson says that when he first set up LAPS and took it to the PFA, he thought they would be supportive, because he designed it for all of the different player unions to use themselves.
I was aware that they had their own recruitment page, and they were a bit dismissive of it. It has been difficult for the PFC.
It's disappointing because I feel that we can achieve so much more without their help. We'll keep trying and hopefully we'll get there someday.
LAPS was formed to tackle the transition from sports person to ordinary member of the public, with a second company formed to help with lifestyle financial planning.
Football players are often given a lot of money at a young age, with no idea how to use it. A football career is a short one and most of the time the money will not last forever because they build a lifestyle that they have the funds to finance at the time.
He doesn't want to impose lifestyle restrictions on clients, but he does want to give a helping hand.
If you're seen to be wanting to move for more money, you're seen to be a bad person. He says there is a stigma there.
Sports people get paid well for what they do, which is what we all want to do. There is a lifestyle demand of a footballer and it takes a strong person to not give in to that.
The first meeting I'll have with a client is just a coffee to see if we get on and if we can trust each other. I like to get an overview of their whole picture, which includes their family, savings, investments, and pension provisions.
We look at short-term, medium-term and long-term. We gauge what they want to do and then come up with a plan and I teach them how to use different financial investment products.
I don't like doing it to limit the lifestyle they want to live now because I feel like it's a burden on them and every time they invest money, it's restrictive." I sit down with them every six months to see how their income changes. Being able to adapt to clients' situations is the key to being a good long-term financialplanner.
The two businesses that keep Simpson involved in professional football continue to grow and offer the footballers of today the support and guidance he found to be absent earlier during his professional career
He admits helping others has changed him personally for the better, and that the whole ethos of both LAPS andRS19 has developed into something much bigger, too, as they tackle mental health issues in sport.
He says that it has made him want to help people.
Setting up LAPS made me less selfish. In the last three years of my career, I became a better player because I was more of a team player.
I used to watch Jordan Rhodes on the bench in hopes that he wouldn't help me. I have never met a nicer person than Jordan Rhodes. I was a bad person back then. I think you can see how much I have grown if you compare my career to the beginning.
One aspect of mental health in sports people is their career coming to an end. Sports people's thoughts are influenced by that. They aren't going to get the feeling of walking out onto a pitch or scoring a goal again if they didn't earn a lot of money.
"We feel that, rather than them having mental health issues and then talking about them, we hope that LAps can help provide interests away from sport alongside their sporting career so maybe they don't have to talk at the end."
You have to buy in from the player. I need to help them understand why these two companies are good for them and how to use them properly.
Players should take comfort in the fact that the word of the guidance he and his companies can offer is slowly making its way into dressing rooms.
He is proof that there is life after sports.
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